A novel enantioselective (up to 90% ee) Michael addition of alpha-substituted cyanoacetates to alpha,beta-unsaturated selenones in the presence of bifunctional urea and thiourea organocatalysts has been described. The Michael adducts, containing an all-carbon quaternary stereocenter, have been smoothly converted into synthetically useful polyfunctional compounds by taking advantage of the excellent leaving group ability of the selenone group.
Enantioselective Organocatalytic Michael Addition of alpha-Substituted Cyanoacetates to alpha,beta-Unsaturated Selenones.
MARINI, Francesca
;STERNATIVO, Silvia;DEL VERME, FRANCESCA;TESTAFERRI, Lorenzo;TIECCO, Marcello
2009
Abstract
A novel enantioselective (up to 90% ee) Michael addition of alpha-substituted cyanoacetates to alpha,beta-unsaturated selenones in the presence of bifunctional urea and thiourea organocatalysts has been described. The Michael adducts, containing an all-carbon quaternary stereocenter, have been smoothly converted into synthetically useful polyfunctional compounds by taking advantage of the excellent leaving group ability of the selenone group.File in questo prodotto:
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